My carry-on only packing  challenge was easy when I was traveling during warm weather. Summer clothes are a cinch to pack. But what about packing for cold weather? Can it be done with bulky winter clothes? Can it be done without wearing the same clothes every other day?

I decided to see if my beloved Tortuga backpack was up for the challenge. First I laid out what I wanted to wear and what I visualized would fit into the pack.

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A variety of tops + a very warm thermal top which turns any blouse into winter-ready attire.

For this challenge I needed 2 weeks worth of outfits (which really is over a month’s worth), workout clothes, and winter accessories. Above is:

  • 1 sweatshirt
  • 2 thin sweaters
  • 1 wrap top
  • 2 shells
  • 2 button-down blouses
  • 1 thermal top from REI

Below is:

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A variety of pants for traveling

In addition to the standard undergarments, PJs, robe, and compression socks, I added thin but warm thermal underwear from Lands End:

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Undergarments, sleepwear, and thermals.


Because I like to stay fit when traveling, I packed one set of workout gear. I would probably trade these trainers for my black leather cross trainers because those can double as casual shoes and are very warm.

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Gotta be prepared for a workout.

The shoes are Inov8 cross training shoes, workout leggings and sports bra by Victoria Secret Sport, tee by Livesore, socks and bandana are from wherever.

I saved my heavy duty coat for wearing on the plane and packed a lighter down jacket for everyday use. Missing are the gloves. There are more packable scarves than the Burberry, but it’s my luxury item that I’ve had for many years. And it’s very, very warm.

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Packable cold-weather outerwear

Here’s what everything looks like packed inside of the bag. The outerwear is packed outside of the bag.

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A carry-on bag full of winter clothes.
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Extra pockets are empty. There’s space for flat items only.
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Outerwear (including down jacket) in the outer pocket
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All zipped up and ready to go.

One outer pocket holds the baggie of liquids while the other holds my 12-oz Klean Canteen.

As for my makeup, jewelry, and other toiletries, they will have to go into my personal item, a gorgeous B&D bag that I got at a consignment shop. I threw my full makeup bag into my tote as a space filler. In a real packing situation, I would use travel-sized toiletries and a much smaller, more flexible bag. I love my newest purse which holds quite a bit and has a detachable bag which can be a small crossbody purse or waist pack. Other items going into the tote: iPad, camera, phone, snacks, and last-minute things I always insist on adding.

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Things that will go into my tote.
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Inside the tote
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Tortuga Backpack and B&D leather tote: ready for winter travel

Following the rule of wearing the bulkiest items, here’s what I’d wear while traveling:

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Travel clothes. Wearing the bulkiest.
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Winter outerwear

The UGG boots and the Lands End parka will keep me very warm in all kinds of frigid temperatures. If the climate is not going to be terribly cold or rainy, I’d trade this and the packable down jacket with a longer packable down coat that I have. When in doubt, though, I’d go with this parka because it provides protection against cold, snow, and rain.

So, the verdict is-

YES! I can do carry-on only year round.  Winter weather does not mean having to check a bag.